Palladium(II)-Catalyzed Intramolecular Diamination of Alkynes under Aerobic Oxidative Conditions: Catalytic Turnover of an Iodide Ion

被引:133
作者
Yao, Bo [1 ]
Wang, Qian [1 ]
Zhu, Jieping [1 ]
机构
[1] Ecole Polytech Fed Lausanne, EPFL SB ISIC LSPN, CH-1015 Lausanne, Switzerland
基金
瑞士国家科学基金会;
关键词
alkynes; diaminations; domino reactions; heterocycles; indole; N-BU4NI-INDUCED ELECTROPHILIC CYCLIZATION; TRANSITION-METAL CATALYSIS; ONE-POT SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; CONJUGATED DIENES; TERMINAL ALKYNES; CRYPTOLEPIS-SANGUINOLENTA; UNACTIVATED ALKENES; ASSISTED SYNTHESIS; MEDIATED SYNTHESIS;
D O I
10.1002/anie.201201640
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
I did it: A sequential intramolecular amination/N- demethylation/amidation of internal acetylenes in the presence of a catalytic amount of Pd(OAc)2 and nBu4NI afforded indolo[3,2-c]isoquinolinones under mild aerobic conditions (see scheme, DMSO=dimethyl sulfoxide). The iodide ion was regenerated by reaction of in situ generated MeI with HOAc present in the reaction mixture. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:5170 / 5174
页数:5
相关论文
共 96 条
[1]   Catalytic arylations with challenging substrates: From air-stable HASPO preligands to indole syntheses and C-H-bond functionalizations [J].
Ackermann, Lutz .
SYNLETT, 2007, (04) :507-526
[2]   A simple, two-step synthesis of 3-iodoindoles [J].
Amjad, M ;
Knight, DW .
TETRAHEDRON LETTERS, 2004, 45 (03) :539-541
[3]  
[Anonymous], 2009, Angew. Chem
[4]  
[Anonymous], 2010, ANGEW CHEM INT EDIT, DOI DOI 10.1002/ANGE.201003499
[5]  
Arcadi A, 2001, SYNLETT, P1605
[6]   PALLADIUM-CATALYZED COUPLING OF ARYL AND VINYL TRIFLATES OR HALIDES WITH 2-ETHYNYLANILINE - AN EFFICIENT ROUTE TO FUNCTIONALIZED 2-SUBSTITUTED INDOLES [J].
ARCADI, A ;
CACCHI, S ;
MARINELLI, F .
TETRAHEDRON LETTERS, 1989, 30 (19) :2581-2584
[7]   New synthesis of benzo-δ-carbolines, cryptolepines, and their salts:: In vitro cytotoxic, antiplasmodial, and antitrypanosomal activities of δ-caribolines, benzo-δ-carbolines, and cryptolepines [J].
Arzel, E ;
Rocca, P ;
Grellier, P ;
Labaeïd, M ;
Frappier, F ;
Guéritte, F ;
Gaspard, C ;
Marsais, F ;
Godard, A ;
Quéguiner, G .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (06) :949-960
[8]   Pd-assisted multicomponent synthesis of heterocycles [J].
Balme, G ;
Bossharth, E ;
Monteiro, N .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (21) :4101-4111
[9]   Pd(II)-catalyzed intermolecular 1,2-diamination of conjugated dienes [J].
Bar, GLJ ;
Lloyd-Jones, GC ;
Booker-Milburn, KI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (20) :7308-7309
[10]   Recent Advances in the Synthesis of Indole and Quinoline Derivatives through Cascade Reactions [J].
Barluenga, Jose ;
Rodriguez, Felix ;
Fananas, Francisco J. .
CHEMISTRY-AN ASIAN JOURNAL, 2009, 4 (07) :1036-1048